US20210195910A1 - Method for decolorization and deodorization of egg yolk oil - Google Patents
Method for decolorization and deodorization of egg yolk oil Download PDFInfo
- Publication number
- US20210195910A1 US20210195910A1 US16/898,480 US202016898480A US2021195910A1 US 20210195910 A1 US20210195910 A1 US 20210195910A1 US 202016898480 A US202016898480 A US 202016898480A US 2021195910 A1 US2021195910 A1 US 2021195910A1
- Authority
- US
- United States
- Prior art keywords
- egg yolk
- yolk oil
- ether solution
- decolorization
- deodorization
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 210000002969 egg yolk Anatomy 0.000 title claims abstract description 188
- 102000002322 Egg Proteins Human genes 0.000 title claims abstract description 185
- 108010000912 Egg Proteins Proteins 0.000 title claims abstract description 185
- 235000013345 egg yolk Nutrition 0.000 title claims abstract description 185
- 238000000034 method Methods 0.000 title claims abstract description 71
- 238000004042 decolorization Methods 0.000 title claims abstract description 22
- 238000004332 deodorization Methods 0.000 title claims abstract description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 104
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 238000003756 stirring Methods 0.000 claims abstract description 39
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000012153 distilled water Substances 0.000 claims abstract description 20
- 238000004821 distillation Methods 0.000 claims abstract description 10
- 238000013019 agitation Methods 0.000 claims description 6
- 238000007796 conventional method Methods 0.000 claims description 2
- 239000003921 oil Substances 0.000 description 141
- 230000000052 comparative effect Effects 0.000 description 26
- 238000001514 detection method Methods 0.000 description 14
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 10
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical class [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 7
- 235000013601 eggs Nutrition 0.000 description 7
- 238000010411 cooking Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000009172 bursting Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000002398 materia medica Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
- A23D7/02—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by the production or working-up
- A23D7/04—Working-up
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L15/00—Egg products; Preparation or treatment thereof
- A23L15/30—Addition of substances other than those covered by A23L15/20 – A23L15/25
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
- A23L5/27—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption
- A23L5/273—Removal of unwanted matter, e.g. deodorisation or detoxification by chemical treatment, by adsorption or by absorption using adsorption or absorption agents, resins, synthetic polymers, or ion exchangers
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/30—Physical treatment, e.g. electrical or magnetic means, wave energy or irradiation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/006—Refining fats or fatty oils by extraction
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/10—Refining fats or fatty oils by adsorption
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/12—Refining fats or fatty oils by distillation
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/04—Colour
- A23V2200/046—Discolouring, bleaching
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2300/00—Processes
- A23V2300/38—Multiple-step
Definitions
- the present invention relates to a method for decolorization and deodorization of egg yolk and a product therefrom, and particularly to a method for preparing high-purity egg yolk oil and a product therefrom.
- Egg yolk oil is the yolk lipid extracted from egg yolk, and also a traditional and ancient product that is mentioned in “Materia Medica” to have “the efficacy of treating wound inflammation, and sorehead by orally taking and external application”. Some products available from Japan are said to have health care effect. If the traditional method for preparing egg yolk oil can be improved or a new egg yolk oil product can be developed, it will be helpful for the diversified use of egg products. Egg products can also be introduced to the health food field, to increase the commercial value of egg products and enhance the industry revenue.
- the traditional egg yolk oil is produced by slowly cooking the egg yolk with slow fire.
- This is referred to as the cooking method, and mainly includes putting the raw material fresh egg yolk into a pot; stirring and frying by heating with low heat until the egg yolk is stirred evenly and equally heated to gradually becomes granular; then crushing the gradually granulated egg yolk, and allowing the water to evaporate to become large particles; continuing to stir with very low heat when the egg yolk changes from golden yellow to dark brown and starts to produce strong burnt smell and thick smoke with continuous stirring, until the particles appear sticky, and a black liquid oozes out, that is, egg yolk oil.
- the yield of the cooking method is about 10%, and the yield is also related to the experience and skills of stir-frying. It is said that those with good stir-frying skills can achieve an egg yolk oil yield of 15% or more with this method.
- the production technology for egg yolk oil by cooking has a very good yield to some extent, it is difficult to control the yield and quality of the product due to the dependence on the experience and skills of stir-frying. Therefore, the method cannot be used in large-scale production on line in factories.
- egg yolk oil can also be prepared by extraction.
- the method mainly includes cooking the egg yolk raw material by heating, adding 5 times of an ethanol solution, mixing thoroughly by stirring, allowing to stand for about 24 h, and then evaporating the ethanol phase, to obtain an egg yolk oil extract.
- the egg yolk oil produced by the cooking method or extraction method is further filtered or centrifuged to remove the residue to obtain a more pure egg yolk oil.
- the present invention provides a method for decolorization and deodorization of egg yolk oil and a product therefrom.
- the strong egg odor and obvious yolk yellow color of the egg yolk oil are removed by means of an ether solution and distilled water, thereby widening the industrial applications of egg yolk oil.
- the present invention discloses a method for decolorization and deodorization of egg yolk oil, and the method comprises at least the following steps: providing a crude egg yolk oil; providing a first ether solution, adding the first ether solution to the crude egg yolk oil, and performing a first stirring process, to produce a first egg yolk oil mixture; providing an activated carbon, adding the activated carbon to the first egg yolk oil mixture, performing a second stirring process, and then removing the activated carbon, to produce a second egg yolk oil mixture; providing a second ether solution and distilled water, adding the second ether solution and distilled water to the second egg yolk oil mixture, and performing a third stirring process, to produce a third egg yolk oil mixture; and distilling the third egg yolk oil mixture to remove distilled water, part of the first ether solution, and part of the second ether solution, and then removing the remaining first ether solution and the remaining second ether solution by a vacuum process to produce a decolorized and deodorized egg yolk oil.
- the present invention further discloses a decolorized and deodorized egg yolk oil.
- the decolorized and deodorized egg yolk oil is prepared through the method for decolorization and deodorization of egg yolk oil.
- the decolorized and deodorized egg yolk oil of the present invention is colorless and odorless, and has an appearance that is close to the white color of the commercially available purified horse oil. That is, the decolorized and deodorized egg yolk oil of the present invention conforms to the standards for commercial sales for use.
- FIG. 1 is a flow chart of the method according to the present invention
- FIG. 2 is a 1 H NMR spectrum for the detection of an egg yolk oil in Comparative Example 1;
- FIG. 3 is a 1 H NMR spectrum for the detection of an egg yolk oil in Comparative Example 2;
- FIG. 4 is a 1 H NMR spectrum for the detection of an egg yolk oil in Example 1;
- FIG. 5 is a 1 H NMR spectrum for the detection of an egg yolk oil in Example 2.
- FIG. 6 shows comparison of 1 H NMR spectra for the detection of egg yolk oils in Example 1 and Comparative Example 1;
- FIG. 7 shows comparison of 1 H NMR spectra for the detection of egg yolk oils in Example 2 and Comparative Example 2;
- FIG. 8 shows comparison of the colors of the egg yolk oils in Example 1 and Comparative Example 1 with horse oil.
- FIG. 1 is a flow chart of the method according to the present invention.
- the present invention discloses a method for decolorization and deodorization of egg yolk oil, and the method includes at least the following steps: providing a crude egg yolk oil 10 ; providing a first ether solution 11 , adding the first ether solution 11 to the crude egg yolk oil 10 , and performing a first stirring process 12 , to fully mix the first ether solution 11 and the crude egg yolk oil 10 to produce a first egg yolk oil mixture 13 ; a decolorization step including: providing an activated carbon 14 that can be made into granules, strips or flakes to increase the contact reaction area of the activated carbon 14 , adding the activated carbon 14 to the first egg yolk oil mixture 13 , performing a second stirring process 15 to fully mix the activated carbon 14 and the first egg yolk oil mixture 13 and allow the activated carbon 14 to fully adsorb the color of the first egg yolk oil mixture 13 , and then removing the activated carbon 14 by conventional filtration, to produce a
- the crude egg yolk oil 10 is commercially available or can be prepared from egg yolk by a conventional method.
- the weight ratio of the first ether solution 11 to the crude egg yolk oil 10 is 5:1, and preferably 3:1.
- the first stirring process 12 is stirring in an agitation tank that may be a sample flask or a barrel, at a rotation speed of 60-155 rpm for 3-5 min.
- the weight ratio of the activated carbon 14 to the first egg yolk oil mixture 13 is 1:3-1:8, and preferably 1:6.
- the second stirring process 15 is stirring in an agitation tank that may be a sample flask or a barrel, at a rotation speed of 60-155 rpm for 3-5 min.
- the weight ratio of the second ether solution 17 to the second egg yolk oil mixture 16 is 5:1, and preferably 3:1.
- the weight ratio of the distilled water 18 to the second egg yolk oil mixture 16 is 7:1, and preferably 10:1.
- the third stirring process 19 is simply stirring in an agitation tank that may be a sample flask or a barrel, for example by rotating 1-2 rounds at a non-restricted speed or shaking the agitation tank for 10-60 s, so that an upper and a lower layer of liquid are still present.
- the distillation process 21 is distillation at a temperature of 60 to 80 degrees Celsius for 30 to 40 min, and preferably at a temperature of 60 to 70 degrees Celsius for 30 to 40 min.
- the vacuum process 22 is treatment under vacuum at a temperature of 20 to 50 degrees Celsius under a pressure of 5 torr for 60-120 min, and preferably at a temperature of 20 to 30 degrees Celsius under a pressure of 5 torr for 70-120 min.
- the present invention further discloses a decolorized and deodorized egg yolk oil 23 .
- the decolorized and deodorized egg yolk oil 23 is prepared through the method for decolorization and deodorization of egg yolk oil.
- a traditionally well-known technique for the manufacture of egg yolk oil was adopted. 1 g of the egg yolk raw material cooked by heating was provided, and 5 ml of an ethanol solution was added, mixed thoroughly by stirring, and allowed to stand for about 24 h. Then the ethanol phase was evaporated, to obtain a crude egg yolk oil extract, that is, the egg yolk oil in Comparative Example 1.
- a traditionally well-known technique for the manufacture of egg yolk oil was adopted. 1 g of an additional egg yolk raw material cooked by heating was provided, and 5 ml of an ethanol solution was added, mixed thoroughly by stirring, and allowed to stand for about 24 h. Then the ethanol phase was evaporated, to obtain a crude egg yolk oil extract, that is, the egg yolk oil in Comparative Example 2.
- the sample flask containing the third egg yolk oil mixture was heated. After about 20 min of heating, the third egg yolk oil mixture reached a temperature of about 70° C., and the third egg yolk oil mixture was constantly maintained at such a temperature of about 70° C. In this case, it is to be noted that the heating source should be turned on/off repeatedly to prevent the third egg yolk oil mixture from exceeding 70° C. and bursting out of the sample flask. This procedure lasted for about 20 min, during which distilled water and ether distilled out were continuously collected and removed. This was a distillation process. Subsequently, the sample flask was removed from the heating source, and left to cool at room temperature. After standing for about 10 min, the solution was poured into a separatory funnel, and the mixture of water and egg yolk oil was separated with the separatory funnel. The separated egg yolk oil mixture was collected in a sample flask.
- the sample flask was fitted on a vacuum concentrator (Model N-1100 series vacuum concentrator), and treated under vacuum at a temperature of about 35° C. under a pressure of about 5 torr for about 120 min.
- the first ether solution and the second ether solution are discharged and removed by evacuation. This was a vacuum process.
- the decolorized and deodorized egg yolk oil in the sample flask is the egg yolk oil in Example 1 of the present invention.
- the sample flask containing the third egg yolk oil mixture was heated. After about 20 min of heating, the third egg yolk oil mixture reached a temperature of about 64° C., and the third egg yolk oil mixture was constantly maintained at such a temperature of about 64° C.
- the heating source should be turned on/off repeatedly to prevent the third egg yolk oil mixture from exceeding 70° C. and bursting out of the sample flask. This procedure lasted for about 20 min, during which distilled water and ether distilled out were continuously collected and removed. This was a distillation process. Subsequently, the sample flask was removed from the heating source, and left to cool at room temperature. After standing for about 10 min, the solution was poured into a separatory funnel, and the mixture of water and egg yolk oil was separated with the separatory funnel. The separated egg yolk oil mixture was collected in a sample flask.
- the sample flask was fitted on a vacuum concentrator (Model N-1100 series vacuum concentrator), and treated under vacuum at a temperature of about 25° C. under a pressure of about 5 torr for about 114 min.
- the first ether solution and the second ether solution are discharged and removed by evacuation. This was a vacuum process.
- the decolorized and deodorized egg yolk oil in the sample flask is the egg yolk oil in Example 2 of the present invention.
- FIG. 2 is a 1 H NMR spectrum for the detection of an egg yolk oil in Comparative Example 1.
- FIG. 2 is a 1 H NMR spectrum for the detection of an egg yolk oil in Comparative Example 1.
- FIG. 3 is a 1 H NMR spectrum for the detection of an egg yolk oil in Comparative Example 2.
- FIG. 4 is a 1 H NMR spectrum for the detection of an egg yolk oil in Example 1.
- FIG. 5 is a 1 H NMR spectrum for the detection of an egg yolk oil in Example 2.
- FIG. 6 shows comparison of 1 H NMR spectra for the detection of egg yolk oils in Example 1 and Comparative Example 1.
- FIG. 7 shows comparison of 1 H NMR spectra for the detection of egg yolk oils in Example 2 and Comparative Example 2.
- FIG. 7 shows that the egg yolk oil of Comparative Example 2 differs in composition from that of the egg yolk oil of Example 2, indicating that some components are definitely removed from the egg yolk oil of Example 2.
- FIG. 8 shows comparison of the colors of the egg yolk oils in Example 1 and Comparative Example 1 with horse oil.
- the product on the left of FIG. 8 is commercially available purified horse oil
- the product in the middle of FIG. 8 is the egg yolk oil of Example 1
- the product on the right of FIG. 8 is the egg yolk oil of Comparative Example 1.
- the egg yolk oil is visually observed to have obviously a white color.
- the olfaction tests of the egg yolk oil of Example 1, the egg yolk oil of Comparative Example 1, the egg yolk oil of Example 2, and the egg yolk oil of Comparative Example 2 were conducted. The results show that the egg yolk oils in Comparative Example 1 and Comparative Example 2 still have strong egg odor, and the egg yolk oils in Example 1 and Example 2 are odor free.
- the present invention can completely decolorize and deodorize the egg yolk oil.
Abstract
Description
- This application claims the benefits of Taiwan application Serial No. 108148504, filed on Dec. 31, 2019, the disclosures of which are incorporated by references herein in its entirety.
- The present invention relates to a method for decolorization and deodorization of egg yolk and a product therefrom, and particularly to a method for preparing high-purity egg yolk oil and a product therefrom.
- Egg yolk oil is the yolk lipid extracted from egg yolk, and also a traditional and ancient product that is mentioned in “Materia Medica” to have “the efficacy of treating wound inflammation, and sorehead by orally taking and external application”. Some products available from Japan are said to have health care effect. If the traditional method for preparing egg yolk oil can be improved or a new egg yolk oil product can be developed, it will be helpful for the diversified use of egg products. Egg products can also be introduced to the health food field, to increase the commercial value of egg products and enhance the industry revenue.
- The traditional egg yolk oil is produced by slowly cooking the egg yolk with slow fire. This is referred to as the cooking method, and mainly includes putting the raw material fresh egg yolk into a pot; stirring and frying by heating with low heat until the egg yolk is stirred evenly and equally heated to gradually becomes granular; then crushing the gradually granulated egg yolk, and allowing the water to evaporate to become large particles; continuing to stir with very low heat when the egg yolk changes from golden yellow to dark brown and starts to produce strong burnt smell and thick smoke with continuous stirring, until the particles appear sticky, and a black liquid oozes out, that is, egg yolk oil.
- The yield of the cooking method is about 10%, and the yield is also related to the experience and skills of stir-frying. It is said that those with good stir-frying skills can achieve an egg yolk oil yield of 15% or more with this method. Although the production technology for egg yolk oil by cooking has a very good yield to some extent, it is difficult to control the yield and quality of the product due to the dependence on the experience and skills of stir-frying. Therefore, the method cannot be used in large-scale production on line in factories.
- It is traditionally well-known for the manufacture of egg yolk oil that egg yolk oil can also be prepared by extraction. The method mainly includes cooking the egg yolk raw material by heating, adding 5 times of an ethanol solution, mixing thoroughly by stirring, allowing to stand for about 24 h, and then evaporating the ethanol phase, to obtain an egg yolk oil extract.
- The egg yolk oil produced by the cooking method or extraction method is further filtered or centrifuged to remove the residue to obtain a more pure egg yolk oil.
- However, although the egg yolk oil production technologies have a fairly good yield to some extent, the product still has a strong egg odor and appears obviously yolk yellow, so that an industrial applicability thereof is greatly limited. The problems need to be overcome.
- In view of this, in order to solve the above problems, the present invention provides a method for decolorization and deodorization of egg yolk oil and a product therefrom. The strong egg odor and obvious yolk yellow color of the egg yolk oil are removed by means of an ether solution and distilled water, thereby widening the industrial applications of egg yolk oil.
- The present invention discloses a method for decolorization and deodorization of egg yolk oil, and the method comprises at least the following steps: providing a crude egg yolk oil; providing a first ether solution, adding the first ether solution to the crude egg yolk oil, and performing a first stirring process, to produce a first egg yolk oil mixture; providing an activated carbon, adding the activated carbon to the first egg yolk oil mixture, performing a second stirring process, and then removing the activated carbon, to produce a second egg yolk oil mixture; providing a second ether solution and distilled water, adding the second ether solution and distilled water to the second egg yolk oil mixture, and performing a third stirring process, to produce a third egg yolk oil mixture; and distilling the third egg yolk oil mixture to remove distilled water, part of the first ether solution, and part of the second ether solution, and then removing the remaining first ether solution and the remaining second ether solution by a vacuum process to produce a decolorized and deodorized egg yolk oil.
- The present invention further discloses a decolorized and deodorized egg yolk oil. The decolorized and deodorized egg yolk oil is prepared through the method for decolorization and deodorization of egg yolk oil.
- The decolorized and deodorized egg yolk oil of the present invention is colorless and odorless, and has an appearance that is close to the white color of the commercially available purified horse oil. That is, the decolorized and deodorized egg yolk oil of the present invention conforms to the standards for commercial sales for use.
-
FIG. 1 is a flow chart of the method according to the present invention; -
FIG. 2 is a 1H NMR spectrum for the detection of an egg yolk oil in Comparative Example 1; -
FIG. 3 is a 1H NMR spectrum for the detection of an egg yolk oil in Comparative Example 2; -
FIG. 4 is a 1H NMR spectrum for the detection of an egg yolk oil in Example 1; -
FIG. 5 is a 1H NMR spectrum for the detection of an egg yolk oil in Example 2; -
FIG. 6 shows comparison of 1H NMR spectra for the detection of egg yolk oils in Example 1 and Comparative Example 1; -
FIG. 7 shows comparison of 1H NMR spectra for the detection of egg yolk oils in Example 2 and Comparative Example 2; and -
FIG. 8 shows comparison of the colors of the egg yolk oils in Example 1 and Comparative Example 1 with horse oil. -
-
- 10 crude egg yolk oil
- 11 first ether solution
- 12 first stirring process
- 13 first egg yolk oil mixture
- 14 activated carbon
- 15 second stirring process
- 16 second egg yolk oil mixture
- 17 second ether solution
- 18 distilled water
- 19 third stirring process
- 20 third egg yolk oil mixture
- 21 distillation process
- 22 vacuum process
- 23 decolorized and deodorized egg yolk oil
- Exemplary embodiments of the present invention will be described below with reference to the accompanying drawings. However, the present invention may alternatively include different forms, and shall not be interpreted as being limited to the embodiments set forth herein. More specifically, these embodiments are provided for completely disclosing the present invention and will fully convey the scope of the present invention to those skilled in the art.
- Hereinafter, the method for decolorization and deodorization of egg yolk oil according to the embodiments of the present invention will be described in detail.
-
FIG. 1 is a flow chart of the method according to the present invention. Referring toFIG. 1 , the present invention discloses a method for decolorization and deodorization of egg yolk oil, and the method includes at least the following steps: providing a crudeegg yolk oil 10; providing afirst ether solution 11, adding thefirst ether solution 11 to the crudeegg yolk oil 10, and performing afirst stirring process 12, to fully mix thefirst ether solution 11 and the crudeegg yolk oil 10 to produce a first eggyolk oil mixture 13; a decolorization step including: providing an activatedcarbon 14 that can be made into granules, strips or flakes to increase the contact reaction area of the activatedcarbon 14, adding the activatedcarbon 14 to the first eggyolk oil mixture 13, performing asecond stirring process 15 to fully mix the activatedcarbon 14 and the first eggyolk oil mixture 13 and allow the activatedcarbon 14 to fully adsorb the color of the first eggyolk oil mixture 13, and then removing the activatedcarbon 14 by conventional filtration, to produce a second eggyolk oil mixture 16; providing asecond ether solution 17 and distilledwater 18, adding thesecond ether solution 17 and distilledwater 18 to the second eggyolk oil mixture 16, and performing athird stirring process 19, to produce a third eggyolk oil mixture 20; a deodorization step including: distilling the third eggyolk oil mixture 20 by adistillation process 21, by which the ingredients of egg odor are concentrated in distilledwater 18 after distillation, and removing distilledwater 18, part of thefirst ether solution 11, and part of thesecond ether solution 17; and then removing the remainingfirst ether solution 11 and the remainingsecond ether solution 17 by evacuation by a vacuum process 22 by taking advantage of the volatility of thefirst ether solution 11 and thesecond ether solution 17, to produce a decolorized and deodorized egg yolk oil. The crudeegg yolk oil 10 is commercially available or can be prepared from egg yolk by a conventional method. The weight ratio of thefirst ether solution 11 to the crudeegg yolk oil 10 is 5:1, and preferably 3:1. Thefirst stirring process 12 is stirring in an agitation tank that may be a sample flask or a barrel, at a rotation speed of 60-155 rpm for 3-5 min. The weight ratio of the activatedcarbon 14 to the first eggyolk oil mixture 13 is 1:3-1:8, and preferably 1:6. Thesecond stirring process 15 is stirring in an agitation tank that may be a sample flask or a barrel, at a rotation speed of 60-155 rpm for 3-5 min. The weight ratio of thesecond ether solution 17 to the second eggyolk oil mixture 16 is 5:1, and preferably 3:1. The weight ratio of the distilledwater 18 to the second eggyolk oil mixture 16 is 7:1, and preferably 10:1. Thethird stirring process 19 is simply stirring in an agitation tank that may be a sample flask or a barrel, for example by rotating 1-2 rounds at a non-restricted speed or shaking the agitation tank for 10-60 s, so that an upper and a lower layer of liquid are still present. Thedistillation process 21 is distillation at a temperature of 60 to 80 degrees Celsius for 30 to 40 min, and preferably at a temperature of 60 to 70 degrees Celsius for 30 to 40 min. The vacuum process 22 is treatment under vacuum at a temperature of 20 to 50 degrees Celsius under a pressure of 5 torr for 60-120 min, and preferably at a temperature of 20 to 30 degrees Celsius under a pressure of 5 torr for 70-120 min. - The present invention further discloses a decolorized and deodorized egg yolk oil 23. The decolorized and deodorized egg yolk oil 23 is prepared through the method for decolorization and deodorization of egg yolk oil.
- The present invention is illustrated by the following examples, but the invention is not limited thereto.
- A traditionally well-known technique for the manufacture of egg yolk oil was adopted. 1 g of the egg yolk raw material cooked by heating was provided, and 5 ml of an ethanol solution was added, mixed thoroughly by stirring, and allowed to stand for about 24 h. Then the ethanol phase was evaporated, to obtain a crude egg yolk oil extract, that is, the egg yolk oil in Comparative Example 1.
- A traditionally well-known technique for the manufacture of egg yolk oil was adopted. 1 g of an additional egg yolk raw material cooked by heating was provided, and 5 ml of an ethanol solution was added, mixed thoroughly by stirring, and allowed to stand for about 24 h. Then the ethanol phase was evaporated, to obtain a crude egg yolk oil extract, that is, the egg yolk oil in Comparative Example 2.
- 1 g of crude egg yolk oil that is the egg yolk oil of Comparative Example 1 was provided as a raw material, and added to a sample flask that is a 50 ml round-bottom glass flask having a specification of 27.5×57 mm (diameter×height). 5 ml of a first ether solution was provided, and added to the crude egg yolk oil. The sample flask was positioned on an electromagnetic stirrer, and then a 20 mm magnetic stirrer bar was placed in the sample flask. The stirring was performed by setting a speed of the electromagnetic stirrer at 155 rpm and a time of 4 min. This was the first stirring process. A first egg yolk oil mixture was produced after the first ether solution and the crude egg yolk oil are thoroughly mixed.
- 1.21 g of granular activated carbon was provided and added to the first egg yolk oil mixture, and continuously stirred with a 20 mm magnetic stirrer bar by setting a speed of the electromagnetic stirrer of 90 rpm and a time of 5 min. This was the second stirring process. After the activated carbon was thoroughly mixed with the first egg yolk oil mixture, activated carbon was removed by filtering through a screen, to produce a second egg yolk oil mixture.
- 5 ml of a second ether solution and 7 ml of distilled water were provided, and added to the second egg yolk oil mixture. The sample flask was stirred by shaking slightly for about 30 sec with hand. This was the third stirring process. Then the sample flask was allowed to stand to separate into an upper and a lower layer of liquid to produce a third egg yolk oil mixture.
- The sample flask containing the third egg yolk oil mixture was heated. After about 20 min of heating, the third egg yolk oil mixture reached a temperature of about 70° C., and the third egg yolk oil mixture was constantly maintained at such a temperature of about 70° C. In this case, it is to be noted that the heating source should be turned on/off repeatedly to prevent the third egg yolk oil mixture from exceeding 70° C. and bursting out of the sample flask. This procedure lasted for about 20 min, during which distilled water and ether distilled out were continuously collected and removed. This was a distillation process. Subsequently, the sample flask was removed from the heating source, and left to cool at room temperature. After standing for about 10 min, the solution was poured into a separatory funnel, and the mixture of water and egg yolk oil was separated with the separatory funnel. The separated egg yolk oil mixture was collected in a sample flask.
- Then, the sample flask was fitted on a vacuum concentrator (Model N-1100 series vacuum concentrator), and treated under vacuum at a temperature of about 35° C. under a pressure of about 5 torr for about 120 min. The first ether solution and the second ether solution are discharged and removed by evacuation. This was a vacuum process. The decolorized and deodorized egg yolk oil in the sample flask is the egg yolk oil in Example 1 of the present invention.
- 1 g of crude egg yolk oil that is the egg yolk oil of Comparative Example 2 was provided as a raw material, and added to a sample flask that is a 50 ml round-bottom glass flask having a specification of 27.5×57 mm (diameter×height). 3 ml of a first ether solution was provided, and added to the crude egg yolk oil. The sample flask was positioned on anelectromagnetic stirrer, and then a 20 mm magnetic stirrer bar was placed in the sample flask. The stirring was performed by setting a speed of the electromagnetic stirrer of 70 rpm and a time of 3 min. This was the first stirring process. A first egg yolk oil mixture was produced after the first ether solution and the crude egg yolk oil are thoroughly mixed.
- 0.52 g of granular activated carbon was provided and added to the first egg yolk oil mixture, and continuously stirred with a 20 mm magnetic stirrer bar by setting a speed of the electromagnetic stirrer of 90 rpm and a time of 5 min. This was the second stirring process. After the activated carbon was thoroughly mixed with the first egg yolk oil mixture, activated carbon was removed by filtering through a screen, to produce a second egg yolk oil mixture.
- 3 ml of a second ether solution and 10 ml of distilled water were provided, and added to the second egg yolk oil mixture. The sample flask was stirred by shaking slightly for about 30 sec with hand. This was the third stirring process. Then the sample flask was allowed to stand to separate into an upper and a lower layer of liquid to produce a third egg yolk oil mixture.
- The sample flask containing the third egg yolk oil mixture was heated. After about 20 min of heating, the third egg yolk oil mixture reached a temperature of about 64° C., and the third egg yolk oil mixture was constantly maintained at such a temperature of about 64° C. In this case, it is to be noted that the heating source should be turned on/off repeatedly to prevent the third egg yolk oil mixture from exceeding 70° C. and bursting out of the sample flask. This procedure lasted for about 20 min, during which distilled water and ether distilled out were continuously collected and removed. This was a distillation process. Subsequently, the sample flask was removed from the heating source, and left to cool at room temperature. After standing for about 10 min, the solution was poured into a separatory funnel, and the mixture of water and egg yolk oil was separated with the separatory funnel. The separated egg yolk oil mixture was collected in a sample flask.
- Then, the sample flask was fitted on a vacuum concentrator (Model N-1100 series vacuum concentrator), and treated under vacuum at a temperature of about 25° C. under a pressure of about 5 torr for about 114 min. The first ether solution and the second ether solution are discharged and removed by evacuation. This was a vacuum process. The decolorized and deodorized egg yolk oil in the sample flask is the egg yolk oil in Example 2 of the present invention.
- Detection by 1H NMR Spectroscopy
- The egg yolk oil of Comparative Example 1, the egg yolk oil of Comparative Example 2, the egg yolk oil of Example 1, and the egg yolk oil of Example 2 were respectively detected by 1H NMR spectroscopy.
FIG. 2 ,FIG. 3 ,FIG. 4 ,FIG. 5 ,FIG. 6 , andFIG. 7 are obtained.FIG. 2 is a 1H NMR spectrum for the detection of an egg yolk oil in Comparative Example 1.FIG. 2 is a 1H NMR spectrum for the detection of an egg yolk oil in Comparative Example 1.FIG. 3 is a 1H NMR spectrum for the detection of an egg yolk oil in Comparative Example 2.FIG. 4 is a 1H NMR spectrum for the detection of an egg yolk oil in Example 1.FIG. 5 is a 1H NMR spectrum for the detection of an egg yolk oil in Example 2.FIG. 6 shows comparison of 1H NMR spectra for the detection of egg yolk oils in Example 1 and Comparative Example 1.FIG. 7 shows comparison of 1H NMR spectra for the detection of egg yolk oils in Example 2 and Comparative Example 2. - It can be found through comparison of
FIG. 2 andFIG. 4 that the 2nd to 4th peaks from the right side inFIG. 2 and inFIG. 4 are different. The comparison inFIG. 6 shows that the egg yolk oil of Comparative Example 1 differs in composition from that of the egg yolk oil of Example 1, indicating that some components are definitely removed from the egg yolk oil of Example 1. - It can be found through comparison of
FIG. 3 andFIG. 5 that the 3rd to 5th peaks from the right side inFIG. 3 and inFIG. 5 are different. The comparison inFIG. 7 shows that the egg yolk oil of Comparative Example 2 differs in composition from that of the egg yolk oil of Example 2, indicating that some components are definitely removed from the egg yolk oil of Example 2. - Verification of the Effectiveness of the Decolorization Step
-
FIG. 8 shows comparison of the colors of the egg yolk oils in Example 1 and Comparative Example 1 with horse oil. The product on the left ofFIG. 8 is commercially available purified horse oil, the product in the middle ofFIG. 8 is the egg yolk oil of Example 1, and the product on the right ofFIG. 8 is the egg yolk oil of Comparative Example 1. The egg yolk oil is visually observed to have obviously a white color. - Verification of the Effectiveness of the Deodorization Step
- The olfaction tests of the egg yolk oil of Example 1, the egg yolk oil of Comparative Example 1, the egg yolk oil of Example 2, and the egg yolk oil of Comparative Example 2 were conducted. The results show that the egg yolk oils in Comparative Example 1 and Comparative Example 2 still have strong egg odor, and the egg yolk oils in Example 1 and Example 2 are odor free.
- As shown by the egg yolk oils in Example 1 and Example 2 of the present invention, the present invention can completely decolorize and deodorize the egg yolk oil.
- Although the present invention is described above with reference to the foregoing preferred embodiments, the embodiments are not intended to limit the present invention. A person of ordinary skill in the art may make variations and modifications without departing from the spirit and scope of the present invention, and such equivalent replacements shall still fall within the protection scope of the present invention.
- In summary, the overall combination and features of the present invention have never been seen in similar products, nor have they been disclosed before the application. Since the legal requirements of the Patent Law have been complied with, an application for this invention patent has been filed in accordance with the law.
Claims (11)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
TW108148504A TWI741469B (en) | 2019-12-31 | 2019-12-31 | Methods for a decolorization and deodorization of egg yolk oil |
TW108148504 | 2019-12-31 |
Publications (2)
Publication Number | Publication Date |
---|---|
US20210195910A1 true US20210195910A1 (en) | 2021-07-01 |
US11678677B2 US11678677B2 (en) | 2023-06-20 |
Family
ID=76545751
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/898,480 Active 2041-09-03 US11678677B2 (en) | 2019-12-31 | 2020-06-11 | Method for decolorization and deodorization of egg yolk oil |
Country Status (2)
Country | Link |
---|---|
US (1) | US11678677B2 (en) |
TW (1) | TWI741469B (en) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU1721080A1 (en) * | 1990-03-27 | 1992-03-23 | Волгодонской Филиал Научно-Производственного Объединения "Синтезпав" | Method of producing egg oil |
RU2634430C1 (en) * | 2016-12-22 | 2017-10-30 | Федеральное государственное бюджетное учреждение науки Институт органической и физической химии им. А.Е. Арбузова Казанского научного центра Российской академии наук | Egg oil production method |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1064396C (en) * | 1997-09-04 | 2001-04-11 | 蔺万斯 | Extraction of yolk oil |
CN1451729A (en) * | 2003-03-25 | 2003-10-29 | 江南大学 | Method for extracting yolk oil by enzyme hydrolysis-solvent extraction |
WO2016024283A1 (en) * | 2014-08-12 | 2016-02-18 | Praj Industries Limited | Process for the preparation of triglycerides of epa and dha |
-
2019
- 2019-12-31 TW TW108148504A patent/TWI741469B/en active
-
2020
- 2020-06-11 US US16/898,480 patent/US11678677B2/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SU1721080A1 (en) * | 1990-03-27 | 1992-03-23 | Волгодонской Филиал Научно-Производственного Объединения "Синтезпав" | Method of producing egg oil |
RU2634430C1 (en) * | 2016-12-22 | 2017-10-30 | Федеральное государственное бюджетное учреждение науки Институт органической и физической химии им. А.Е. Арбузова Казанского научного центра Российской академии наук | Egg oil production method |
Non-Patent Citations (9)
Title |
---|
Google search for NPL "Activated Carbon Removal" [Retrieved on 10/21/2022]. (Year: 2022) * |
Google Search for NPL Footbalt (Retrieved on 10/21/2022). (Year: 2022) * |
Google Search for NPL OFI Magazine (Retrieved on 10/21/2022). (Year: 2022) * |
NPL "Activated Carbon Removal" [in Carbon filtration and activated charcoal | Experiment | RSC Education ; See last page -Year 2016]. (Year: 2016) * |
NPL Footbalt et al. ( 2014, pages 2, Chapter by Aleksandrs et al. 253-256] (Year: 2014) * |
NPL Larsen et al. (in Poultry Sci. 60: 160-167, 1980). (Year: 1980) * |
NPL Master Chao et al. (2011: "Egg yolk oil Recipe-Natural Farming Hawaii) (Year: 2011) * |
NPL OFI magazine (2017) [Activated carbon is used in edible oil bleaching to remove ...https://www.ofimagazine.com. news › Activated…] (Year: 2017) * |
NPL Wu et al. ( in Molecules vol 21, 106, 2016: Molecules 2016, 21, 106; doi:10.3390/molecules 21010106). (Year: 2016) * |
Also Published As
Publication number | Publication date |
---|---|
TWI741469B (en) | 2021-10-01 |
US11678677B2 (en) | 2023-06-20 |
TW202126798A (en) | 2021-07-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102807918B (en) | Original-fragrant camellia oil rich in active components and producing method thereof | |
CN104789350B (en) | Aromatous camellia oil of health and safety with rich flavor and preparation method thereof | |
JPS6152656B2 (en) | ||
TW201032724A (en) | Palm oil, deodorized distillates and manufacturing methods therefor | |
CN113845971A (en) | Flavored beef tallow and preparation method thereof | |
US9506011B2 (en) | Method and composition for producing a stable and deodorized form of pomegranate seed oil | |
CN108165363A (en) | A kind of preparation process of low color-value giving off a strong fragrance rapeseed oil | |
US11678677B2 (en) | Method for decolorization and deodorization of egg yolk oil | |
US5243059A (en) | Process for preparing refined palm oil | |
KR101394644B1 (en) | Method for Preparing Low Bound 3-MCPD Edible Oil | |
KR100502960B1 (en) | additive by use of vinaigre and method for producing the same | |
JP4365260B2 (en) | Production of rapeseed flavor oil | |
UA127792C2 (en) | Edible oil refining | |
CN105238557A (en) | Antioxidative refined lard oil | |
EP3213639B1 (en) | Extract emulsified oil comprising antioxidant, edible oil containing same, and preparation method therefor | |
CN109233999A (en) | A kind of preparation method of original fragrant vegetable seed oil | |
JP5901136B2 (en) | Luo oil and fat and ruo using the same | |
JPS6136724B2 (en) | ||
JP2006075117A (en) | Method for producing far-infrared ray-roasted sesame oil, far-infrared ray-roasted sesame oil and sesame oil blended with the roasted sesame oil | |
CN108299495A (en) | The edible phospholipid that a kind of production method of edible phospholipid and production obtain | |
US2454937A (en) | Process of treating glyceride oils with activated magnesium oxide | |
CA3125514A1 (en) | Apparatus and methods for processing coffee grounds | |
NL8203695A (en) | PROCESS FOR PREPARING PEANUT OIL. | |
KR101498284B1 (en) | The olive oil compound and the method for manufacturing the filtered olive oil | |
KR101044129B1 (en) | Method for Lard cooking oil |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: TAMKANG UNIVERSITY, TAIWAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CHEN, YAU-HUNG;CHERN, MING-KAI;TSAI, TUNG-HAN;AND OTHERS;SIGNING DATES FROM 20200430 TO 20200514;REEL/FRAME:052902/0994 |
|
FEPP | Fee payment procedure |
Free format text: ENTITY STATUS SET TO UNDISCOUNTED (ORIGINAL EVENT CODE: BIG.); ENTITY STATUS OF PATENT OWNER: SMALL ENTITY |
|
FEPP | Fee payment procedure |
Free format text: ENTITY STATUS SET TO SMALL (ORIGINAL EVENT CODE: SMAL); ENTITY STATUS OF PATENT OWNER: SMALL ENTITY |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: NON FINAL ACTION MAILED |
|
STCF | Information on status: patent grant |
Free format text: PATENTED CASE |